US8710244B2 - Dyes and methods of marking biological material - Google Patents

Dyes and methods of marking biological material Download PDF

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Publication number
US8710244B2
US8710244B2 US13/728,859 US201213728859A US8710244B2 US 8710244 B2 US8710244 B2 US 8710244B2 US 201213728859 A US201213728859 A US 201213728859A US 8710244 B2 US8710244 B2 US 8710244B2
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Prior art keywords
dye
biological material
independently selected
chemical formula
mixtures
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US13/728,859
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US20130344499A1 (en
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Shin-Shin Wang
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Industrial Technology Research Institute ITRI
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Industrial Technology Research Institute ITRI
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Assigned to INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE reassignment INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: WANG, SHIN-SHIN
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B11/00Diaryl- or thriarylmethane dyes
    • C09B11/04Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10Amino derivatives of triarylmethanes
    • C09B11/24Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/52Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/58Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
    • G01N33/582Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances with fluorescent label
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S436/00Chemistry: analytical and immunological testing
    • Y10S436/80Fluorescent dyes, e.g. rhodamine

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Hematology (AREA)
  • Immunology (AREA)
  • Organic Chemistry (AREA)
  • Urology & Nephrology (AREA)
  • Biomedical Technology (AREA)
  • Molecular Biology (AREA)
  • Food Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Cell Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Biotechnology (AREA)
  • Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
US13/728,859 2012-06-22 2012-12-27 Dyes and methods of marking biological material Active US8710244B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
TW101122353A TWI468469B (zh) 2012-06-22 2012-06-22 染料與標記生物材料的方法
TW101122353 2012-06-22
TW101122353A 2012-06-22

Publications (2)

Publication Number Publication Date
US20130344499A1 US20130344499A1 (en) 2013-12-26
US8710244B2 true US8710244B2 (en) 2014-04-29

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US13/728,859 Active US8710244B2 (en) 2012-06-22 2012-12-27 Dyes and methods of marking biological material

Country Status (3)

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US (1) US8710244B2 (zh)
CN (1) CN103509366B (zh)
TW (1) TWI468469B (zh)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE49362E1 (en) 2006-05-18 2023-01-10 Illumina Cambridge Limited Dye compounds and the use of their labelled conjugates
WO2019068804A1 (fr) * 2017-10-04 2019-04-11 Unisensor Dispositif de lecture optique à la carte d'un support solide amovible pour la détection et/ou la quantification d'analytes présents dans un échantillon

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6130101A (en) * 1997-09-23 2000-10-10 Molecular Probes, Inc. Sulfonated xanthene derivatives
US6383749B2 (en) 1999-12-02 2002-05-07 Clontech Laboratories, Inc. Methods of labeling nucleic acids for use in array based hybridization assays
US6448407B1 (en) 2000-11-01 2002-09-10 Pe Corporation (Ny) Atropisomers of asymmetric xanthene fluorescent dyes and methods of DNA sequencing and fragment analysis
US6750357B1 (en) * 1999-06-25 2004-06-15 Syngen, Inc. Rhodamine-based fluorophores useful as labeling reagents
EP2036897A1 (en) 2007-09-04 2009-03-18 Roche Diagnostics GmbH Stable rhodamine labeling reagent
US20100197030A1 (en) 2009-02-03 2010-08-05 Biotium, Inc. Xanthene dyes comprising a sulfonamide group
US20100209354A1 (en) 2007-10-01 2010-08-19 Centre National De La Recherche Scientifique - Cnrs Organic/inorganic hybrid nanoparticulates made from iron carboxylates
US20100226991A1 (en) 2007-10-01 2010-09-09 Centre National De La Recherche Scientifique - Cnrs- Solid inorganic/organic hybrid with modified surface
WO2011029459A1 (en) 2009-09-10 2011-03-17 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Novel photoactivable fluorescent dyes for optical microscopy and image techniques

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6323337B1 (en) * 2000-05-12 2001-11-27 Molecular Probes, Inc. Quenching oligonucleotides

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6130101A (en) * 1997-09-23 2000-10-10 Molecular Probes, Inc. Sulfonated xanthene derivatives
US6750357B1 (en) * 1999-06-25 2004-06-15 Syngen, Inc. Rhodamine-based fluorophores useful as labeling reagents
US6383749B2 (en) 1999-12-02 2002-05-07 Clontech Laboratories, Inc. Methods of labeling nucleic acids for use in array based hybridization assays
US20060188915A1 (en) 2000-11-01 2006-08-24 Applera Corporation Atropisomers of asymmetric xanthene fluorescent dyes and methods of dna sequencing and fragment analysis
US6649769B2 (en) 2000-11-01 2003-11-18 Applera Corporation Atropisomers of asymmetric xanthene fluorescent dyes and methods of DNA sequencing and fragment analysis
US7038063B2 (en) 2000-11-01 2006-05-02 Applera Corporation Atropisomers of asymmetric xanthene fluorescent dyes and methods of DNA sequencing and fragment analysis
US6448407B1 (en) 2000-11-01 2002-09-10 Pe Corporation (Ny) Atropisomers of asymmetric xanthene fluorescent dyes and methods of DNA sequencing and fragment analysis
US20070254298A1 (en) 2000-11-01 2007-11-01 Applera Corporation, Applied Biosystems Group Atropisomers of asymmetric xanthene fluorescent dyes and method of dna sequencing and fragment analysis
EP2036897A1 (en) 2007-09-04 2009-03-18 Roche Diagnostics GmbH Stable rhodamine labeling reagent
US20100209354A1 (en) 2007-10-01 2010-08-19 Centre National De La Recherche Scientifique - Cnrs Organic/inorganic hybrid nanoparticulates made from iron carboxylates
US20100226991A1 (en) 2007-10-01 2010-09-09 Centre National De La Recherche Scientifique - Cnrs- Solid inorganic/organic hybrid with modified surface
US20100197030A1 (en) 2009-02-03 2010-08-05 Biotium, Inc. Xanthene dyes comprising a sulfonamide group
WO2011029459A1 (en) 2009-09-10 2011-03-17 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Novel photoactivable fluorescent dyes for optical microscopy and image techniques

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Boyarskiy et al., "Photostable, Amino Reactive and Water-Soluble Fluorescent Labels Based on Sulfonated Rhodamine with a Rigidized Xanthene Fragment", Chemistry a European Journal, 2008, 14, pp. 1784-1792.
Liu et al., "Rational design and synthesis of a novel class of highly fluorescent rhodamine dyes that have strong absorption at long wavelengths", Tetrahedron Letters, 2003, 44, pp. 4355-4359.
Meng et al., "Synthesis of N-hydroxysuccinimidyl benzoate and its structural insight into labeling activity of fluorescent probes", Dyes and Pigments, 2007, 75, pp. 166-169.
Mujumdar et al., "Cyanine Dye Labeling Reagents Containing Isothiocyanate Groups", Cytometry, 1989, 10, pp. 11-19.
Shandura et al., "New heterocyclic analogues of rhodamines", Dyes and Pigments, 2007, 73, pp. 25-30.

Also Published As

Publication number Publication date
US20130344499A1 (en) 2013-12-26
TWI468469B (zh) 2015-01-11
CN103509366B (zh) 2015-09-30
TW201400551A (zh) 2014-01-01
CN103509366A (zh) 2014-01-15

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